Water → HCID 136377341, compound

HRID 1051799Notes

Reaction equation

HRID 1051799 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=O)=[N:9][C:8]([C@@H:14]([NH:16][C:17]1[N:25]=[CH:24][N:23]=[C:22]3[C:18]=1[N:19]=[CH:20][N:21]3[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[CH3:15])=[CH:7]2.Cl.[NH2:36][OH:37].O>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](/[CH:12]=[N:36]\[OH:37])=[N:9][C:8]([C@@H:14]([NH:16][C:17]1[N:25]=[CH:24][N:23]=[C:22]3[C:18]=1[N:19]=[CH:20][N:21]3[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[CH3:15])=[CH:7]2

Participants

6

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 86665022HCID 86665022, compound

Product 1

HCID 136377341HCID 136377341, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of (S)-8-chloro-3-(1-((9-(4-methoxybenzyl)-9H-purin-6-yl)amino)ethyl)isoquinoline-1-carbaldehyde 5 (270 mg, 0.57 mmol, 1.0 eq) and hydroxylamine hydrochloride (495 mg, 7.1 mmol, 13 eq) in pyridine (4 mL) and MeOH (20 mL) was stirred at RT overnight. The reaction mixture was poured into water (50 mL) and extracted with DCM (3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (1-10% MeOH-DCM) to afford the product, (S,Z)-8-chloro-3-(1-((9-(4-methoxybenzyl)-9H-purin-6-yl)amino)ethyl)isoquinoline-1-carbaldehyde oxime (240).

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (1-10% MeOH-DCM)

Sources & evidence

ORD record
ord-9c21583c7d22455a80dd809697a95e2b
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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